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EP4396256A1 - Stabilisatorkombination zur verhinderung des abbaus von synthetischen polymeren - Google Patents

Stabilisatorkombination zur verhinderung des abbaus von synthetischen polymeren

Info

Publication number
EP4396256A1
EP4396256A1 EP22760754.6A EP22760754A EP4396256A1 EP 4396256 A1 EP4396256 A1 EP 4396256A1 EP 22760754 A EP22760754 A EP 22760754A EP 4396256 A1 EP4396256 A1 EP 4396256A1
Authority
EP
European Patent Office
Prior art keywords
tert
component
butyl
stabilizer
phenyl
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Pending
Application number
EP22760754.6A
Other languages
English (en)
French (fr)
Inventor
Cinzia Tartarini
Raphael Dabbous
Jorge ESPINOS ARIZTI
Guo Liang Yuan
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
BASF SE
Original Assignee
BASF SE
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by BASF SE filed Critical BASF SE
Publication of EP4396256A1 publication Critical patent/EP4396256A1/de
Pending legal-status Critical Current

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    • C08K5/00—Use of organic ingredients
    • C08K5/04—Oxygen-containing compounds
    • C08K5/15—Heterocyclic compounds having oxygen in the ring
    • C08K5/151—Heterocyclic compounds having oxygen in the ring having one oxygen atom in the ring
    • C08K5/1535—Five-membered rings
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    • C08K5/00—Use of organic ingredients
    • C08K5/0008—Organic ingredients according to more than one of the "one dot" groups of C08K5/01 - C08K5/59
    • C08K5/005—Stabilisers against oxidation, heat, light, ozone
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    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
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    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/65—Low-molecular-weight compounds having active hydrogen with high-molecular-weight compounds having active hydrogen
    • C08G18/66—Compounds of groups C08G18/42, C08G18/48, or C08G18/52
    • C08G18/6666—Compounds of group C08G18/48 or C08G18/52
    • C08G18/667—Compounds of group C08G18/48 or C08G18/52 with compounds of group C08G18/32 or polyamines of C08G18/38
    • C08G18/6681—Compounds of group C08G18/48 or C08G18/52 with compounds of group C08G18/32 or polyamines of C08G18/38 with compounds of group C08G18/32 or C08G18/3271 and/or polyamines of C08G18/38
    • C08G18/6688—Compounds of group C08G18/48 or C08G18/52 with compounds of group C08G18/32 or polyamines of C08G18/38 with compounds of group C08G18/32 or C08G18/3271 and/or polyamines of C08G18/38 with compounds of group C08G18/3271
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    • C08G18/74—Polyisocyanates or polyisothiocyanates cyclic
    • C08G18/76—Polyisocyanates or polyisothiocyanates cyclic aromatic
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Definitions

  • the present invention relates to a composition
  • a composition comprising polyether polyol or polyurethane (PU), as component (i), and as component (ii) a stabilizer combination based on (ii.1 ) a benzofuranone derivative such as a 3-Phenyl-benzofuran-2-one derivative, (ii .2) a sterically hindered phenol such as a bisphenolic stabilizer, and (ii .3) an aliphatic phosphorous (III) compound such as a phosphite or phosphonate ester.
  • the present composition is suited to prevent oxidative, thermal or light- induced degradation of a synthetic polymer.
  • the current invention relates as well to a process for manufacturing the aforementioned composition, the use of the specific stabilizer combination (ii) for stabilizing the component (i)
  • An objective of this present invention is to describe a novel anti-scorch composition based on a benzofuranones, an sterically hindered phenol and an aliphatic phosphorous (III) compound preferably in liquid form, which provides scorch protection, low emissions according to stringent automotive emissions standards as well as reduction of aldehyde emissions from Polyol and PU foams.
  • Another advantageous feature is a low PU foams discoloration upon storage when using the novel stabilizer compositions according to the present invention.
  • the current invention relates to a composition
  • a composition comprising as component (i) a synthetic polymer selected from a polyurethane foam or a polyether polyol, and as component (ii) a ternary stabilizer combination comprising as component (ii.1 ) at least a substituted benzofuranone derivative, preferably a 3-Phenyl-benzofuran-2-one derivative, component (ii .2) at least one sterically hindered phenol, preferably a bisphenolic stabilizer, and component (ii.3) at least an aliphatic phosphorous (III) compound, preferably an aliphatic phosphite (di)ester compound.
  • component (i) a synthetic polymer selected from a polyurethane foam or a polyether polyol
  • a ternary stabilizer combination comprising as component (ii.1 ) at least a substituted benzofuranone derivative, preferably a 3-Phenyl-benzofuran-2-one derivative
  • EP 1291384 discloses the application of a benzofuranone substituted with an acetoxy-substi- tuted phenyl as depicted below as a stabilizer of a polyurethane foam based on a polyether polyol. It is found superior regarding discoloration of the stabilized foam versus a comparative benzofuranone substituted with a phenyl, which is solely substituted by two Ci-alklyl groups, as depicted below.
  • DPDP liquid aromatic diphenyl isodecyl phosphite
  • both benzofuranones are applied as stabilizer of a polyether polyol and a similar performance is described for both.
  • Reported examples include one polymeric lactone in combination with sterically hindered phenol, aromatic amine and UV absorber. However, no combinations with phosphites are specifically described.
  • WO 2015/121445 discloses benzofuranone phosphite derivatives as a stabilizer for organic materials susceptible to oxidative, thermal or light-induced degradation. Usually the benzofuranone phosphites described are applied for stabilization of polyethylene or polypropylene. Inter alia, two specific mono-benzofuranone phosphites as depicted below are employed.
  • So-called sterically hindered phenols are known in the industry since long time. These are for instance those phenols which attached to the aromatic ring have exactly one phenolic hydroxy group and particularly preferably around such, those that in the ortho positions, most preferably in the ortho- and para-position to the phenolic hydroxy group have a substituent, preferably an alkyl group, in particular to alkyl-3- (3,5-di-tert-butyl-4-hydroxyphenyl) propionate, respectively to substituted alkyl derivatives of such compounds. Their effects are based on steric hindrance, which is a consequence of steric effects.
  • Organic compounds of trivalent phosphorous such as phosphites or phosphonates are often used as hydroperoxide decomposers, through their oxidation to phosphate derivatives.
  • Phosphites are known as antioxidants in the industry since long time and several patents describe their use as secondary stabilizers, however in most of the cases these are of aromatic origin and in solid form. For instance, phosphites have been described in combination with sterically hindered phenols.
  • WO 2019/057539 describes the use of di-octyl phosphonate, which is of aliphatic origin and in liquid form, reporting the use in polyisocyanate compositions.
  • water is preferably added to the reaction mixture prior to the reaction in an amount from 0.5 to 12 parts by weight based on 100 parts by weight of the polyol reactant. More preferably, 1 to 8 parts of water are added. Most preferably, 2 to 7 parts of water are added, for example 3 to 7 or 4 to 7 parts of water. Particularly for a polyure- thane foam having a density between 16 and 32 kg/m 3 , 3 to 8 parts water are added. For a polyurethane foam having a density above 32 kg/m 3 and below 48 kg/m 3 , 2 to 5 parts of water are added.
  • R 24 and R 34 are both the same and selected from methyl, ethyl, n-propyl, iso-propyl, n-butyl, sec. -butyl, iso-butyl und tert.-butyl, wherein the alkyl radical may be further substituted with one or more Ci-C4-alkyl radicals.
  • Stabilizer component (1.1-2) is depicted below and obtainable according to example P-2 of WO 2017/025431 A1.
  • Stabilizer component (1.1-5) which is 4-tert-butyl-2-(5-tert-butyl-2-oxo-2,3-dihydro-1-benzofuran- 3-yl)phenyl 3,5-di-tert-butyl-4-hydroxybenzoate and depicted below, is a commercially available as Revonox 501TM.
  • Stabilizer component (II.2-2) is depicted below and is commercially obtainable as Irganox
  • Alkylated monophenols for example 2,6-di-tert-butyl-4-methylphenol, 2-tert-butyl-4,6-di- methylphenol, 2,6-di-tert-butyl-4-ethylphenol, 2,6-di-tert-butyl-4-n-butylphenol, 2,6-di-tert-butyl- 4-isobutylphenol, 2,6-dicyclopentyl-4-methylphenol, 2-(a-methylcyclohexyl)-4,6-dimethylphenol, 2,6-dioctadecyl-4-methylphenol, 2,4,6-tricyclohexylphenol, 2,6-di-tert-butyl-4-methoxymethyl- phenol, nonylphenols which are linear or branched in the side chains, for example 2,6-di-nonyl- 4-methylphenol, 2,4-dimethyl-6-(1 '-methylundec-1 '-yl- 4-
  • Hydroquinones and alkylated hydroquinones for example 2,6-di-tert-butyl-4-methoxyphe- nol, 2,5-di-tert-butylhydroquinone, 2,5-di-tert-amylhydroquinone, 2,6-diphenyl-4-octadecyl-oxy- phenol, 2,6-di-tert-butylhydroquinone, 2,5-di-tert-butyl-4-hydroxyanisole, 3,5-di-tert-butyl-4-hy- droxyanisole, 3,5-di-tert-butyl-4-hydroxyphenyl stearate, bis(3,5-di-tert-butyl-4-hydroxyphenyl) adipate.
  • Tocopherols for example a-tocopherol, p-tocopherol, y-tocopherol, 5-tocopherol and mixtures thereof (vitamin
  • Hydroxylated thiodiphenyl ethers for example 2,2'-thiobis(6-tert-butyl-4-methylphenol), 2,2'- thiobis(4-octylphenol), 4,4'-thiobis(6-tert-butyl-3-methylphenol), 4,4'-thiobis(6-tert-butyl-2- methylphenol), 4,4'-thiobis(3,6-di-sec-amylphenol), 4,4'-bis(2,6-dimethyl-4-hydroxyphenyl)disul- fide.
  • 2,2'-thiobis(6-tert-butyl-4-methylphenol 2,2'- thiobis(4-octylphenol), 4,4'-thiobis(6-tert-butyl-3-methylphenol), 4,4'-thiobis(6-tert-butyl-2- methylphenol), 4,4'-thiobis(3,6-di-sec-amylphenol), 4,4'-bis
  • O-, N- and S-benzyl compounds for example 3,5,3',5'-tetra-tert-butyl-4,4'-dihydroxydibenzyl ether, octadecyl-4-hydroxy-3,5-dimethylbenzylmercaptoacetate, tridecyl-4-hydroxy-3,5-di-tert- butylbenzylmercaptoacetate, tris(3,5-di-tert-butyl-4-hydroxybenzyl)amine, bis(4-tert-butyl-3-hy- droxy-2,6-dimethylbenzyl)dithioterephthalate, bis(3,5-di-tert-butyl-4-hydroxybenzyl)sulfide, iso- octyl-3,5-di-tert-butyl-4-hydroxybenzylmercaptoacetate.
  • Aromatic hydroxybenzyl compounds for example 1 ,3,5-tris(3,5-di-tert-butyl-4-hydroxyben- zyl)-2,4,6-trimethylbenzene, 1 ,4-bis(3,5-di-tert-butyl-4-hydroxybenzyl)-2,3,5,6-tetramethylben- zene, 2,4,6-tris(3,5-di-tert-butyl-4-hydroxybenzyl)phenol.
  • Triazine compounds for example 2,4-bis(octylmercapto)-6-(3,5-di-tert-butyl-4-hydroxyani- lino)-1 ,3,5-triazine, 2-octylmercapto-4,6-bis(3,5-di-tert-butyl-4-hydroxyanilino)-1 ,3,5-triazine, 2- octylmercapto-4,6-bis(3,5-di-tert-butyl-4-hydroxyphenoxy)-1 ,3,5-triazine, 2,4,6-tris(3,5-di-tert- butyl-4-hydroxyphenoxy)-1 ,2,3-triazine, 1 ,3,5-tris(3,5-di-tert-butyl-4-hydroxybenzyl)isocyanurate, 1 ,3,5-tris(4-tert-butyl-3-hydroxy-2,6-dimethylbenzyl)isocyanurate
  • Benzylphosphonates for example dimethyl-2,5-di-tert-butyl-4-hydroxybenzylphosphonate, diethyl-3, 5-di-tert-butyl-4-hydroxybenzylphosphonate, dioctadecyl-3, 5-di-tert-butyl-4-hy- droxybenzylphosphonate, dioctadecyl-5-tert-butyl-4-hydroxy-3-methylbenzylphosphonate, the calcium salt of the monoethyl ester of 3,5-di-tert-butyl-4-hydroxybenzylphosphonic acid, (3,5- ditert-butyl-4-hydroxy-phenyl)methylphosphonic acid.
  • Acylaminophenols for example 4-hydroxylauranilide, 4-hydroxystearanilide, octyl N-(3,5- di-tert-butyl-4-hydroxyphenyl)carbamate.
  • esters of p-(3,5-di-tert-butyl-4-hydroxyphenyl)propionic acid especially with octadecanol, such as the addition of Octadecyl-3-(3,5-di-tert.butyl-4-hydroxyphenyl)-propionate as depicted in formula (V) below. which is a commercially available (e.g. Irganox 1076TM).
  • esters of p-(3,5-dicyclohexyl-4-hydroxyphenyl)propionic acid with mono- or polyhydric alcohols for example with methanol, ethanol, octanol, octadecanol, 1 ,6-hexanediol, 1 ,9-nonane- diol, ethylene glycol, 1 ,2-propanediol, neopentyl glycol, thiodiethylene glycol, diethylene glycol, triethylene glycol, pentaerythritol, tris(hydroxyethyl)isocyanurate, N,N'-bis(hydroxyethyl)ox- amide, 3-thiaundecanol, 3-thiapentadecanol, trimethylhexanediol, trimethylolpropane, 4-hy- droxymethyl-1-phospha-2,6,7-trioxabicyclo[2.
  • esters of 3,5-di-tert-butyl-4-hydroxyphenyl acetic acid with mono- or polyhydric alcohols for example with methanol, ethanol, octanol, octadecanol, 1 ,6-hexanediol, 1 ,9-nonanediol, ethylene glycol, 1 ,2-propanediol, neopentyl glycol, thiodiethylene glycol, diethylene glycol, triethylene glycol, pentaerythritol, tris(hydroxyethyl)isocyanurate, N,N'-bis(hydroxyethyl)oxamide, 3- thiaundecanol, 3-thiapentadecanol, trimethylhexanediol, trimethylolpropane, 4-hydroxymethyl-1- phospha-2,6,7-trioxabicyclo[2.2.2]octane.
  • 2-(2'-Hydroxyphenyl)benzotriazoles for example 2-(2'-hydroxy-5'-methylphenyl)benzotria- zole, 2-(3',5'-di-tert-butyl-2'-hydroxyphenyl)benzotriazole, 2-(5'-tert-butyl-2'-hydroxyphenyl)ben- zotriazole, 2-(2'-hydroxy-5'-(1 ,1 ,3,3-tetramethylbutyl)phenyl)benzotriazole, 2-(3',5'-di-tert-butyl- 2'-hydroxyphenyl)-5-chlorobenzotriazole, 2-(3'-tert-butyl-2'-hydroxy-5'-methylphenyl)-5-chloro- benzotriazole, 2-(3'-sec-butyl-5'-tert-butyl-2'-hydroxyphenyl)benzotriazole, 2-(2'-sec-but
  • Esters of substituted and unsubstituted benzoic acids for example 4-tert-butylphenyl salicylate, phenyl salicylate, octylphenyl salicylate, dibenzoyl resorcinol, bis(4-tert-butylbenzoyl)resor- cinol, benzoyl resorcinol, 2,4-di-tert-butylphenyl 3,5-di-tert-butyl-4-hydroxybenzoate, hexadecyl
  • Nickel compounds for example nickel complexes of 2,2'-thiobis[4-(1 ,1 ,3,3-tetramethyl- butyl)phenol], such as the 1 :1 or 1 :2 complex, with or without additional ligands such as n-butyl- amine, triethanolamine or N-cyclohexyldiethanolamine, nickel dibutyldithiocarbamate, nickel salts of the monoalkyl esters, e.g. the methyl or ethyl ester, of 4-hydroxy-3,5-di-tert-butylbenzyl- phosphonic acid, nickel complexes of ketoximes, e.g. of 2-hydroxy-4-methylphenylundecylke- toxime, nickel complexes of 1-phenyl-4-lauroyl-5-hydroxypyrazole, with or without additional ligands.
  • additional ligands such as n-butyl- amine, triethanolamine or N-cyclohexy
  • Sterically hindered amines for example bis(2,2,6,6-tetramethyl-4-piperidyl)sebacate, bis(2,2,6,6-tetramethyl-4-piperidyl)succinate, bis(1 ,2,2,6,6-pentamethyl-4-piperidyl)sebacate, bis(1 ,2,2,6,6-pentamethyl-4-piperidyl) n-butyl-3,5-di-tert-butyl-4-hydroxybenzylmalonate, the condensate of 1-(2-hydroxyethyl)-2,2,6,6-tetramethyl-4-hydroxypiperidine and succinic acid, linear or cyclic condensates of N,N'-bis(2,2,6,6-tetramethyl-4-piperidyl)hexamethylenediamine and 4-tert-octylamino-2,6-dichloro-1 ,3,5-triazine, tris(2,2,6,6-tetramethyl-4-
  • Oxamides for example 4,4'-dioctyloxyoxanilide, 2,2'-diethoxyoxanilide, 2,2'-dioctyloxy-5,5'- di-tert-butoxanilide, 2,2'-didodecyloxy-5,5'-di-tert-butoxanilide, 2-ethoxy-2'-ethyloxanilide, N,N'- bis(3-dimethylaminopropyl)oxamide, 2-ethoxy-5-tert-butyl-2'-ethoxanilide and its mixture with 2- ethoxy-2'-ethyl-5,4'-di-tert-butoxanilide, mixtures of o- and p-methoxy-disubstituted oxanilides and mixtures of o- and p-ethoxy-disubstituted oxanilides.
  • Metal deactivators for example N,N'-diphenyloxamide, N-salicylal-N'-salicyloyl hydrazine, N,N'-bis(salicyloyl)hydrazine, N,N'-bis(3,5-di-tert-butyl-4-hydroxyphenylpropionyl)hydrazine, 3- salicyloylamino-1 ,2,4-triazole, bis(benzylidene)oxalyl dihydrazide, oxanilide, isophthaloyl dihydrazide, sebacoyl bisphenylhydrazide, N,N'-diacetyladipoyl dihydrazide, N,N'-bis(salicyloyl)oxal- yl dihydrazide, N,N'-bis(salicyloyl)thiopropionyl dihydrazide.
  • Phosphites and phosphonates are required additives of the stabilizer combination according to the present invention.
  • Tris alkyl (C12-C15) phosphite Triisodecyl phosphite, Triisotridecyl phosphite, Dioleyl Hydrogen phosphite, Triisooctyl Phosphite, Heptakis (dipropyleneglycol) Triphosphite, Trilauryl Trithio Phosphite, Tris (Dipropyleneglycol) Phosphite, Dimethyl hydrogen phosphite, Dibutyl hydrogen phosphite, Dilauryl hydrogen phosphite, Tri-C12-C14-phosphite, Bis(2-ethylhexyl) hydrogen phosphite and - especially preferred - liquid phosphites such as Di-n-octyl hydrogen phosphite
  • phosphites and phosphonates which are different to those defined components (ii.3) , but which can be used additionally in the compositions according to the present invention are preferably liquid ones as for example triphenyl phosphite, tris(nonylphenyl) phosphite, Phenyldiisodecyl phosphite, Diphenylisodecyl phosphite, [Triphenyl phosphite, polymer with 1 ,4-cyclohexanedimethanol and polypropylene glycol, C10-16 alkyl esters (CAS Reg. No. 1821217-71-3)].
  • phosphites or phosphonates additives to be mentioned here as well are for instance Alkyl (C12-C15) bisphenol A phosphite, Alkyl (C10) bisphenol A phosphite, Poly (dipropyleneglycol) phenyl phosphite, Tris (tridecyl) phosphite, Diphenyl phosphite, Dodecyl nonylphenol phosphite blend, Phenyl Neopentylene Glycol Phosphite, Poly 4,4' Isopropy- lidenediphenol - C10 Alcohol Phosphite, Poly 4,4' Isopropylidenediphenol - C12-15 Alcohol Phosphite, diphenylalkyl phosphites, phenyldialkyl phosphites, C12-C18 alkyl bis[4-(1-methyl-1- phenyl-ethyl)phenyl] phosphi
  • Hydroxylamines and amine N-oxides for example N,N-dibenzylhydroxylamine, N,N -diethyl hydroxylamine, N,N-dioctylhydroxylamine, N,N-dilaurylhydroxylamine, N,N-ditetradecylhydroxyla- mine, N,N-dihexadecylhydroxylamine, N,N-dioctadecylhydroxylamine, N-hexadecyl-N-octade- cylhydroxylamine, N-heptadecyl-N-octadecylhydroxylamine, N,N-dialkylhydroxylamine derived from hydrogenated tallow amine , N,N-bis-(hydrogenated rape-oil alkyl)-N-methyl-amine N-oxide or trialkylamine N-oxide.
  • Nitrones for example N-benzyl-alpha-phenylnitrone, N-ethyl-alpha-methylnitrone, N-octyl-al- pha-heptylnitrone, N-lauryl-alpha-undecylnitrone, N-tetradecyl-alpha-tridecylnitrone, N-hexa- decyl-alpha-pentadecylnitrone, N-octadecyl-alpha-heptadecylnitrone, N-hexadecyl-alpha-hepta- decylnitrone, N-octadecyl-alpha-pentadecylnitrone, N-heptadecyl-alpha-heptadecylnitrone, N- octadecyl-alpha-hexadecylnitrone, nitrone derived from N
  • Thiosynergists for example dilauryl thiodipropionate, dimistryl thiodipropionate, distearyl thiodipropionate and pentaerythritol tetrakis-[3-(n-lauryl)-propionic acid ester],
  • Peroxide scavengers for example esters of a-thiodipropionic acid, for example the lauryl, stearyl, myristyl or tridecyl esters, mercaptobenzimidazole or the zinc salt of 2-mercaptobenzim- idazole, zinc dibutyldithiocarbamate, dioctadecyl disulfide, pentaerythritol tetrakis(p-dodecylmer- capto)propionate.
  • esters of a-thiodipropionic acid for example the lauryl, stearyl, myristyl or tridecyl esters
  • mercaptobenzimidazole or the zinc salt of 2-mercaptobenzim- idazole zinc dibutyldithiocarbamate
  • dioctadecyl disulfide pentaerythritol tetrakis(p-d
  • Acid scavengers for example melamine, polyvinylpyrrolidone, dicyandiamide, triallyl cyanu- rate, urea derivatives, hydrazine derivatives, alkali metal salts and alkaline earth metal salts of higher fatty acids, for example calcium stearate, zinc stearate, magnesium behenate, magnesium stearate, sodium ricinoleate and potassium palmitate, antimony pyrocatecholate and zinc pyrocatecholate. 10.
  • Acid scavengers for example melamine, polyvinylpyrrolidone, dicyandiamide, triallyl cyanu- rate, urea derivatives, hydrazine derivatives, alkali metal salts and alkaline earth metal salts of higher fatty acids, for example calcium stearate, zinc stearate, magnesium behenate, magnesium stearate, sodium ricinoleate and potassium palmitate, antimony pyrocatecholate and zinc pyrocate
  • Phosphorus containing flame retardants including reactive phosphorous containing flame retardants, for example tetraphenyl resorcinol diphosphite (Fyrolflex RDP, RTM, Akzo Nobel), tetrakis(hydroxymethyl)phosphonium sulphide, triphenyl phosphate, diethyl-N,N-bis(2-hydroxy- ethyl)-aminomethyl phosphonate, hydroxyalkyl esters of phosphorus acids, alkylphosphate oligomers, ammonium polyphosphate (APP), resorcinol diphosphate oligomer (RDP), phosphazene flame retardants or ethylenediamine diphosphate (EDAP).
  • reactive phosphorous containing flame retardants for example tetraphenyl resorcinol diphosphite (Fyrolflex RDP, RTM, Akzo Nobel), tetrakis(hydroxymethyl)phosphonium sulphide, triphenyl phosphat
  • Nitrogen containing flame retardants for example melamine-based flame retardants, iso- cyanurates, polyisocyanurate, esters of isocyanuric acid, like tris-(2-hydroxyethyl)isocyanurate, tris(hydroxymethyl)isocyanurate, tris(3-hydroxy-/7-propyl)isocyanurate, triglycidyl isocyanurate, melamine cyanurate, melamine borate, melamine phosphate, melamine pyrophosphate, melamine polyphosphate, melamine ammonium polyphosphate, melamine ammonium pyrophosphate, dimelamine phosphate, dimelamine pyrophosphate, benzoguanamine, allantoin, glyco- luril, urea cyanurate, a condensation product of melamine from the series melem, melam, melon and/or a higher condensed compound or a reaction product of melamine with phosphoric
  • Organohalogen flame retardants for example polybrominated diphenyl oxide, decabromodiphenyl oxide (DBDPO), tris[3-bromo-2,2-bis(bromomethyl)propyl] phosphate (PB 370, (RTM, FMC Corp.)), tris(2,3-dibromopropyl)phosphate, chloroalkyl phosphate esters such as tris(chlo- ropropyl)phosphate, tris(2,3-dichloropropyl)phosphate, tris(1 ,3-dichloro-2-propyl)phosphate (Fyrol FR 2 (RTM I CL)), oligomeric chloroalkyl phosphate, chlorendic acid, tetrachlorophthalic acid, tetrabromophthalic acid, poly-p-chloroethyl triphosphonate mixture, tetrabromobisphenol A-bis(2,3-dibromopropy
  • halogenated flame retardants mentioned above are routinely combined with an inorganic oxide synergist.
  • Some of the halogentated flame retardants mentioned above can be used in combination with triaryl phosphates (such as the propylated, butylated triphenyl phosphates) and the like and I or with oligomeric aryl phosphates (such as resorcinol bis(diphenyl phosphate), bisphenol A bis(diphenyl phosphate), neopentylglycol bis(diphenyl phosphate)) and the like.
  • triaryl phosphates such as the propylated, butylated triphenyl phosphates
  • oligomeric aryl phosphates such as resorcinol bis(diphenyl phosphate), bisphenol A bis(diphenyl phosphate), neopentylglycol bis(diphenyl phosphate)
  • Inorganic flame retardants for example aluminium trihydroxide (ATH), boehmite (AIOOH), magnesium dihydroxide (MDH), zinc borates, CaCOs, organically modified layered silicates, organically modified layered double hydroxides, and mixtures thereof.
  • ATH aluminium trihydroxide
  • AIOOH boehmite
  • MDH magnesium dihydroxide
  • CaCOs organically modified layered silicates
  • organically modified layered double hydroxides and mixtures thereof.
  • the most common inorganic oxide synergists are zinc oxides, antimony oxides like Sb20s or Sb20s or boron compounds.
  • composition according to the present invention may comprise
  • At least one further additive selected from the group of chromanol antioxidants such as-a-tocopherol, p-tocopherol, /-tocopherol, 5-tocopherol and mixtures thereof (vitamin E), vitamin E acetate; and/or from the group of aromatic aminic antioxidants such as a phenylarylamine, wherein the amine is only substituted with a phenyl and an Ce-C -aryl and the phenyl or the Ce-C -aryl is alkylated; and/or from the group of esters of 3,5-di-tert-butyl-4-hydroxyphenyl acetic acid with mono- or polyhydric alcohols, such as methanol, ethanol, octanol, octadecanol, 1 ,6-hexanediol, 1 ,9-nonanediol, ethylene glycol, 1 ,2-propanediol, neopen
  • composition according to the present invention comprises as further additive (iii) at least one chromanol stabilizer of formula III wherein R 1 -"' and R 2 -"' are independently of each other H or methyl.
  • additives may be added as well, of which especially preferred is Irganox 5057 TM , which is obtained by the reaction of diphenylamine with diisobutylene, and which comprises
  • An especially preferred stabilizer composition comprises the combined stabilizers in the following weight percentages:
  • (iii) preferably a first further additive, which is a technical mixture of aromatic amines obtained by the reaction of diphenylamine with diisobutylene (also commercially available as Irganox 5057TM).
  • the process for manufacturing a composition comprises the step of
  • di-octyl hydrogen phosphite did not show significant antioxidant activity and improvement in binary combinations with the above-mentioned stabilizers.
  • Anti-scorch systems are needed to prevent scorch during the production of flexible PU foams and they are usually introduced in Polyol, one of the main raw materials used for the process. Since polyol and more in particular polyether polyols are prone to thermal degradation, it is important that the anti-scorch system used also provides good stability to Polyol against thermal degradation which may occur during storage and transportation.
  • Example 1 Stabilization of a polyether/polyurethane soft foam
  • Tegostab BF 2370 (RTM Evonik Industries; surfactant based on polysiloxane), 0.18 g Tegoamin 33 (RTM Evonik Industries; general purpose gelling catalyst based on triethylene diamine) and 8.4 g of deionized water are added and the reaction mixture is stirred vigorously for 10 seconds at 2600 rpm. 0.36 g Kosmos 29 (RTM Evonik Industries; catalyst based on stan- nous octoate) dissolved with 3.24 g of Polyol are then added and the reaction mixture is again stirred vigorously for 18 hours at 1400 rpm.
  • isocyanate TDI 80 (mixture containing 80% toluene-2,4- diisocyanate and 20% toluylene-2, 6-diisocyanate isomers) is then added with continuous stirring for 5 to 7 seconds at 2600 rpm. The mixture is then poured into a 20 x 20 x 20 cm plastic-box and an exothermic foaming reaction takes place as indicated by an increase of temperature. The foam buns are cooled and stored at room temperature for 24 hours. All prepared foam buns show a comparable initial white colour and were use, unless otherwise specified, in the following examples.
  • the scorch resistance is assessed by measuring the colour of the foam sample after aging. The measured colour is reported in terms of Yellowness Index (Yl) determined on the foam sample in accordance with the ASTM D 1925-70 Yellowness Test. Low Yl values denote little discoloration, high Yl values severe discoloration of the samples. The whiter a foam sample remains, the better the foam sample is stabilized.
  • Yl Yellowness Index
  • Delta Yl (Discoloration of the PU stabilized formulation) - (Discoloration of the PU non-stabi- lizer formulation)
  • the use of the sterically hindered phenol stabilizer alone does show an anti-scorch performance, whereas the use of the aliphatic phosphorous (III) compound dioctyl hydrogen phosphite alone does even cause a higher discoloration compared to the con- trol.
  • the use of a binary 1 :1 stabilizer combination having the same total concentration of stabilizers as the singly used stabilizer shows a weaker anti-scorch performance, meaning a higher Delta Yl value, than the single use of the sterically hindered phenol stabilizer, and if the ratio is gradually modified in favor of a higher share of the sterically hindered phenol, an improvement of the anti-scorch performance is observed.
  • the lowest Delta Yl valuer is achieved when using the sterically hindered phenol alone.
  • Ternary b > stabilizer combination according to the present invention notes: a > comparative b > according to the invention Part II. Ternary b > stabilizer combination according to the present invention with further additives
  • Polyols especially of polyether type, are prone to thermo-oxidative degradation leading to volatile side-products, including aldehydes.
  • Anti-scorch systems which can prevent degradation should play a role to the released volatile side-products too, reducing their quantity.
  • aldehydes are particularly critical due to their classification and contribution to odor.
  • Asia the industry refers to standards and regulations aiming to reduce the amount of volatile components of aldehyde type.
  • Example A. 7 Emission measurement in PU foams
  • Gas fading resistance is an important secondary property for foams that during storage can undergo discoloration due to interaction with nitrogen oxides present in the atmosphere. Such attitude is determined by exposing the produced foam samples in a chamber with a controlled atmosphere, which contains 4-6 ppm of Nitrogen Oxide.
  • the gas fading resistance is assessed by measuring the color of the foam sample after exposure. The measured color is reported in terms of Yellowness Index (Yl) determined on the foam sample in accordance with the ASTM 1926-70 Yellowness Test. Low Yl values denote little discoloration, high Yl values severe discoloration of the samples. The whiter a foam sample remains, the better the foam sample is stabilized.
  • Yl Yellowness Index
  • Polyurethane Foams widely used on the market are based on aromatic isocyanate and as such tend to discolor under exposure to light during storage and end use. Such characteristic is determined under laboratory conditions by exposing the produced foam samples in a chamber with controlled temperature and humidity, and with a light source mimicking sunlight radiation.
  • Xenon lamps are widely used in accelerated so-called “weathering” due to the similarity of their light spectrum to the sunlight spectrum.

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